


Maid in Waiting

by jenfoxworth



Series: Tis time for Paperhat ya'll! [1]
Category: Villainous (Cartoon)
Genre: Black Hat is a kinky bastard, Crossdressing, Eventual Smut, Flug stands up for himself kinda sorta not really, M/M, Maid Dr. Flug, Master/Servant, Paper Hat - Freeform, Paperhat - Freeform, Smut, Smut starts in chapter 2
Language: English
Status: In-Progress
Published: 2017-10-08
Updated: 2017-11-13
Packaged: 2019-01-10 21:53:38
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,069
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12308574
Author URL: https://archiveofourown.org/users/jenfoxworth/pseuds/jenfoxworth
Summary: Flug gets one day off every month, but to him it's not really a day off. He finally says something about it, and gets more then he bargained for... He finds out WHY his Boss puts him in a frilly maid outfit...!





	1. Servant for the day

[](http://tinypic.com?ref=2mo30aa)

"FLUG, HURRY UP WITH THAT WINE, I DON'T HAVE ALL DAY!" Flug heard his bosses impatient yell from the other room. The scientist rolled his eyes as he tried to go faster, reaching for Black Hat's special signature wine from the top shelf. He was certain that it was put all the way up here just to make it harder to get, because of course if the demon wanted it, he only had to manifest a tentacle to reach for it.

Climbing down carefully from the ladder, Flug grumbled at how much more difficult it was to move around in this absurd outfit. The boss gave him one day off from lab work a month, but it wasn't really a day off. It was more of a day for the boss to have off, since Flug was put in this ridiculous black, white, and red maid outfit that Black Hat had gotten for him. The demon had insisted it was because 505 was getting the same day off, and wouldn't be cleaning, so Flug got to do it. Surely it's not anywhere near as difficult as lab work, easy light cleaning for just one day a month is certainly like a day off for you, his boss had told him.

Yeah, sure it is, thought Flug, while also tending to Black Hat's every whim. He was getting really sick of this, he'd been doing it for three years already, once every month! Shining his bosses shoes, making sure no fuzz got on his suit and hat, having to follow him everywhere to make sure things were not in his way, and in case he wanted wine or anything else. 

"FLUUUUUUUUUUUUGGGG!!!" The voice was turning even deeper and more demonic. Fixing his ruffles a bit, dusting them off, Flug moved quickly with his serving tray. Entering the office he saw his boss was impatiently drumming his fingers with one hand on the desk, leaning on his other with a hand on the side of his face.

"S-sorry, sir-..." Flug started.

"IT'S ABOUT TIME, I MEAN GOD DAMN! YOU'D THINK HAVING A DAY OFF WOULD GIVE YOU ENOUGH REST TO BE FASTER, BUT NOOOOO.... DECIDED TO TAKE YOUR TIME WITH DOING EVEN A SIMPLE TASK!" Black Hat said angrily.

The scientist in the frilly maid outfit quivered in his red stockings as he tried to get the wine open. Wasn't easy with such shaky, nervous hands. After hearing an exasperate sigh from the other, he managed to somehow get it open and poured the wine. Before he could set the wine glass down his boss reached for it. The thought of Black Hat touching him at the moment terrified him so much that he jerked away from the motion, and dropped the drink, the glass shattering with the blood red wine all over the carpet. 

"YOU CLUMSY IDIOT!!!" 

Flug didn't even dare to look at his boss, he immediately started to clean up the mess, but cried out in pain when the demon stepped on his hands, crushing them into the mess of glass and alcohol. 

"P-P-PLEASE S-SIR!!" He cried, it was cutting through his silk maid gloves into his hands. Surprisingly, his boss complied, released his hands and allowed him to finish cleaning it up, for the most part. Flug had put the mess onto the tray and was about to carry it out to get rid of it, and attempt to doctor his hands up as fast as he could before he was immediately called back again of course...

"Put. The. Tray. Down." The scientist quivered, and did as he was told, still not looking at his boss, head down. Even though the anger had drained from the voice, he wasn't about to get his hopes up, he knew better.

"Look at me, you idiot!" Flug looked up slowly, only to see exactly what he expected. The voice hadn't been angry, not more then usual, but the glare from the expression revealed it.

"Tell me, Flug. How is it that on your day off, you can be so clumsy? You aren't even in the lab! This should be fairly easy for you, don't you think?! Or do you want to go back to your lab?! I mean you're the one who wanted the bear to get a day off too, since he seemed to be getting tired so often!" The demon demanded, arms crossed over his chest in severe disappointment.

The human was still shaking in fear. He was so sick of this. Day off?! DAY OFF?! THIS WASN'T A DAY OFF!! HE WAS CLUMSY BECAUSE HE WAS TERRIFIED!!!

"ANSWER!" 

"I-I-I..." Flug started.

"AND DON'T LIE, I CAN TELL IF YOU DO, IF I EVEN THINK FOR A MOMENT YOU ARE, I'LL GET INTO THAT HEAD OF YOURS TONIGHT WHEN YOU'RE SLEEPING AND FIND OUT, AND YOUR PUNISHMENT WILL BE SEVERE!"

The scientist knew full well not to take the threat lightly, he had carried it out in full before, the demon was fully capable of entering ones mind when they were either unconscious or sleeping.

".... I.... I'm.... I'm clumsy because I'm scared...."

The demon raised an eyebrow in suspicion.

"It... It isn't really... A d-d-day off... I'm stuck waiting on y-you, it's still s-s-stressful!" Flug could feel tears starting to form in his eyes, and tried to fight them back, wouldn't be a good idea to show too much weakness at a time like this.

"505's d-d-day off and m-m-my d-d-day off should be on s-s-separate days!" He finished, still struggling not to cry, and failing.

"So, that's what you think, is it?" Flug looked up in surprise, still quivering. His boss's face was still stern, as always, but it didn't look so mad anymore.

"Y-y...yes..."

"Okay then. Fine. Your actual day off will be tomorrow, and the bear's will be today." The demon said, not showing any change in emotion. 

"R-really?!" It was impossible to read the demon's face, with it so blank, his true intentions were a mystery.

"D-did I s-stutter, Flug?!" Black Hat mocked him.

"N-no, sir, of course not...!"

"Then get your ass over here, NOW!" He demanded.

The scientist stepped forward, still surprised, confused, and ever so slightly hopeful that this would turn out a little better then he had expected. Maybe he wasn't going to be punished so harshly... But for his boss to grant him a request usually meant a consequence before hand... 

"Close your eyes, idiot."

Flug complied, fear creeping back into him quickly. Without warning, he felt his bag and goggles being yanked off, and he whimpered. He... needed... he needed that bag...! He felt the maid ribbons being put back carefully on his head, without his bag. A gloved hand suddenly touched his face, softly, followed by a dark snicker.

"Haven't seen your face in a while, doctor... You're always hiding those lovely freckles and scars!"

The human kept his eyes closed, he hadn't been ordered to open them yet, but he was again surprised. Lovely? What?! He bit his lip. He was making fun of him... Of course, that had to be it.

Suddenly he felt firm hands on his waist, lifting him up and placing him to sit on the edge of the desk. He didn't struggle, but was now even more confused as to what was going on.

"Scars as deep as that... Turn me on!" Flug's eyes shot open at this, WHAT?!

Before he could even respond, the demon had grabbed him, and pulled him into a rough kiss. The scientist was frozen, a hundred emotions running through his mind, putting him shock.

"Ha... You're speechless already, Flug?!" The boss using his actual name snapped him out of his confused daze. The demon's face was satisfied looking, though he saw a tiny, hidden amount of uncertainty. 

"I... I..." Flug couldn't even speak. He had no idea what he could even say. Was this even... real...?! Had that just really happened?! HAD HIS DEMON BOSS JUST KISSED HIM?! He completely forgot about his bag being taken, BECAUSE WHAT EVEN THE HELL...?!

"Want another?" Black Hat asked, raising a slanted eyebrow.

Before the scientist could even think about it, he responded with a nod. Wait... WHAT?!  
The demon was on him again in an instant, any uncertainty seeming to have faded completely. Not that there had been much to begin with. This time, as Black Hat pulled him closer, Flug slowly started to put his arms around him, almost terrified to do so, wondering if he was even allowed to touch him of his own accord.

The eldritch felt his touch and kissed him harder, deepening it with forcing his forked tongue into the human's mouth. Flug moaned at this, apparently he was. Black Hat pulled him even closer, so that Flug's legs were on either side of him. He paused for a split second, to allow the human to breath. 

"You fool... your taste is intoxicating...!" The demon growled at him.

Again, he wasn't allowed to reply as he was forced into the kiss again, one of the demons hands behind his head, digging with his claws into the red, curly locks, guiding his subject so he could get better angles. 

Flug dare not put his own tongue into his bosses mouth, not with his bear trap teeth at the entrance... He didn't really have to though, since the demon was controlling most of his movements with his head, the long tongue reaching all the areas of his mouth before sliding down his throat. As this happened, Flug felt one of the clawed hands playing with the ruffles of the maid outfit, lifting them up so it could slide up his thigh, forming a long thin, bloody scratch as it grazed his skin.

A frightened, but aroused whimper came from the scientist. At this, Black Hat growled in his heat, and pulled out of the reckless kiss, saliva threading between their lips as he suddenly grabbed both of the doctor's hands and slammed him down onto his back on the desk. There was a primal fierceness in the eldritch's eye now. He licked his sharp teeth.

"I'm going to FUCK YOU... SO HARD... FLUG!!!"

There was a pause in the moment, the human's mind racing. Oh god... Was this really happening?! Could he say no?! Why would you want to say no.... WAIT WHAT WAS HE EVEN THINKING...?! Getting fucked by Black Hat could very well kill him, who knows what the demon would do to him!


	2. Polite does not mean gentle

**Summary for the Chapter:**

> Welp, there goes that lovely dress of his!  
> Short chapter but eh, the pic makes up for it.  
> You better like that pic, I worked hard on it!  
> Drools all over the pic. :p.......

[ ](http://tinypic.com?ref=358xxf4)

Black Hat was still standing there over Flug, breathing heavily. Had the scientist just heard correctly?! Slimy, green, translucent drool dripped from the demons mouth as he licked his sharp teeth again. His eye narrowed as he glared at his target.

Flug was trembling violently by now. His mind going a million miles a minute, he couldn't figure out what to do, say, or if he was even supposed to do any of those things. He was still pinned to the desk by his wrists.

The demon appeared to be savoring the moment, going slow. "Today is not your day off, doctor, so you must do as I say!" the eldritch growled at him.

By now Flug was nearly hyperventilating. Did that mean he couldn't say no, that whatever his boss wanted was going to happen anyway? Was he going to fuck him to death, so he didn't have to worry about days off, and just find another scientist or something? What did this mean, what was he planning?! The scientist couldn't figure it out, and gave a nervous swallow, tears starting to form in his eyes again.

"Ooooohhh! You look so lovely when you're terrified! You really should see the face you're making, it's grand!" The beast chuckled darkly.  
Flug didn't know how to respond to that either, so he just whimpered a little.

His boss started to lean down to him; terrified, Flug closed his eyes, and waited. The demon's hot breath was on his neck, and he felt the tongue slip briefly into his ear before retreating back into it's maw. A shudder ran through him uncontrollably at that point, reacting.  
"Well...?"

Nothing was happening. Not anything more anyway, the situation was still the same. Flug was still to scared to speak, he barely managed a questioning squeak.

"I'm not going to ask again, your next response will be my answer, and if it's something incomprehensible then it will be your own fault!" Now the demon started to look irritated and impatient. Flug suddenly realized that he was asking permission to fuck him. Albeit in a very rude and disturbing way, but still...

"It's not polite to keep someone waiting...!" Black Hat warned him, fang-like teeth grazing his neck again with a huff, his growl deepening.  
The cross-dressed maid for the day wasn't sure what to say. Running the options again in his mind, yes or no... If he said no, the demon might very well kill him, if not he would certainly punish him for earlier if nothing else, and it would be painful. If he said yes... A quiver ran through him again as he thought about it. He might die from that experience as well. So either way...

"Fuck me then."

Black Hat's eye widened in delighted surprise, then narrowed maliciously again, accompanied by a hiss.

"It would be my pleasure!" The demon released his grip so that he could snap his fingers, the office door slamming closed and locking automatically. The drapes on the windows fell as well, and it became quite dark, though not quite pitch black, just severely dimmed. Flug heard him remove his jacket, at this, the scientist wondered what HE was allowed to do, or if he was just supposed to be there for the 'ride'.... just an object of satisfaction... He wasn't sure.

"S-sir..?" He dared a question. Another impatient growl, but the demon waited.

"A-am... W-will... I be... r-required...?" Flug couldn't finish, he was too nervous, but the other could guess at what he was thinking.

"If you desire to you may, but you best know your limits, pet!" With that the human was pressed into another kiss, though this one was slower, more meaningful.

And damn, did it turn Flug on. He gave a muffled moan as his boss's clawed hands began to slide up his frilled skirt again, the gloves were off too.  
Hesitating for just a moment, Flug reached up and undid the others necktie, along with starting to unbutton his shirt, hoping that was allowed. The response he was given was clear, when the tongue went into his mouth again. 

The demon pressed his body against him, grinding their hips together in a humping motion. A noticeable bulge pressed against his own sensitive area. One of the hands slid further up to his waist, while the other began to pull at his undergarments.

"Oh ho ho! You're even wearing the laced panties! How adorable!" 

"Y-you said I h-had to wear the entire outfit!" Flug stuttered, his face going an even deeper shade of red.

"You were wise not to disobey...!" The demon snickered at him as he slid his claws under to grasp the doctor's now thickening member.

The human gave a startled gasp of pleasure as he squeezed it, gently at first, allowing his claws to graze the sensitive tip. Flug arched into it, instinctively wanting more. With that, the demon removed the underwear entirely, not bothering to pull them down, but gave a flick of the wrist to rip them off.  
There was a brief rush of cold air on his privates, but it was quickly gone as his boss pressed them together again, and this time there was no barrier from either side. He wasn't entirely sure what he was feeling, though it hadn't entered him yet, and it was wet, whatever it was.

"O-o-ooohh...!" Flug's response was cut off from another kiss, this one not so gentle, teeth cutting into his lips. Strangely enough the roughness of it seemed to stimulate him even more, his hands on Black Hat's waist, trying to pull him closer. 

"Who's the impatient one now?" His boss teased, continuing to run his claws all over the other's body, shredding the outfit into ribbons as he did so, leaving shallow cuts in their wake.

The human pulled on him more, but the demon backed off a bit, growling and digging his claws into the scientist's now vulnerable hips. 

"Eager little pet... don't make me get out the leash and choke collar! Behave!" One of the hands went to Flug's throat, and gave it a warning squeeze.

The scientist gulped and released his grip, holding onto the desk instead. He was incorrect however, this wasn't what the demon wanted, who tightened his grip, slowly starting to suffocate him. 

"Guess again!"

Flug felt his vision start to blur as he got dizzy from the lack of air. He was confused, but knew he better try something else, he didn't know if his boss would actually be willing to kill him or not, but even if he didn't...

This time Flug's hands went to the demon's chest, not to push him away, but to attempt to caress him. The hold on his neck loosened, air rushing back into his lungs, though this made him even dizzier for a moment.

"Better...! Now, pet, let's see what you can endure!" The eldritch's hands went to Flug's thighs, spreading his legs apart. Before Flug could respond he pinned him again, knowing full well this would be painful, as he had several tentacle dicks, some of them with barbs on them.

Pressing his body down over him again, his prehensile members began to slowly force their way into him, first one, then a second... not bothering to prepare him first.

The scientist whimpered loudly, clenching his teeth, but otherwise didn't move.

"Oh, you're being such a good boy... Trying so hard!" The demon's tongue slithered out again and licked his neck. At this point he allowed a third and fourth one to enter him, stretching him even farther, and what was more, these two were barbed.

A noise halfway between a scream and a mangled sob came from him, but still he didn't struggle. 

"Shhh, pet.....! It hurts... doesn't it?" Black Hat halted for the moment, letting the human have a brief respite before he turned up the heat.

**Notes for the Chapter:**

> I'm going to hell for this ain't I.  
> Oh wait, I don't believe in hell.  
> Jumps into the sin bin and uses it as a jacuzzi.  
> YEAHHHHHHH BABY!!!
> 
> It's midnight and I've lost my mind!

**Author's Note:**

> Ohhhhh Flugggggg... Is this punishment, or a reward, we'll have to wait and see. Either way, we'll like it, won't we!


End file.
